US2794038A - Halogenated mercurisulfonates - Google Patents
Halogenated mercurisulfonates Download PDFInfo
- Publication number
- US2794038A US2794038A US405657A US40565754A US2794038A US 2794038 A US2794038 A US 2794038A US 405657 A US405657 A US 405657A US 40565754 A US40565754 A US 40565754A US 2794038 A US2794038 A US 2794038A
- Authority
- US
- United States
- Prior art keywords
- mercurisulfonates
- halogenated
- hexachlorobicyclo
- heptene
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- QQCRUPWXPBONTC-UHFFFAOYSA-N 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl QQCRUPWXPBONTC-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- -1 ethyl mercuri acetate Chemical compound 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 241001645342 Diaporthe citri Species 0.000 description 1
- 241000935926 Diplodia Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241001480007 Phomopsis Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241000194062 Xanthomonas phaseoli Species 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Definitions
- This invention relates to a new fungicidal composition of matter. Specifically, the present invention relates to -(p-ethylmercurisulfonylphenyl) 1,2,3,4,7,7 hexachlorobicyclo-(2.2.1)-2-heptene having the structure:
- composition of the present invention is useful in low concentrations of from 5 to 25 parts per million in controlling tomatoe anthracnose (Colletotrichum phamoides), watermelon end rot (Diplodia natelen sis), barley stripe disease (Helminthosporium gramineum), citrus stem rot (PhomOpsis citri), tomatoe early blight (Alternaria solani), and crown and root rot of alfalfa and soybeans (Rhizoctonia solani).
- the product of the present invention may be prepared from sulfonyl chlorides or sulfonyl fluorides of S-phenyll,2,3,4,7,7-hexachlorobicyclo-(2.2.1 -2-heptene described in the copending application of Percy B. Polen, Serial No. 405,658, filed Jan. 22, 1954, now Patent No. 2,712,030.
- Such sulfonyl halides are treated with sodium acetate to prepare the sodium salt and the sodium salt reacted with ethyl mercuri acetate or any ethyl mercun' salt to form the ethyl mercuri sulfonate compound of the present invention.
- the following specific example will illustrate the preparation of the present product:
- a mixture comprising 47.5 g. (0.1 mole) of 5-(pchlorosulfonylphenyl) 1,2,3,4,7 ,7 hexachlorobicyclo- (2.2.1)-2-heptene, 100 ml. glacial acetic acid, and 16 g. (0.2 mole) of sodium acetate was heated at reflux for three hours. The inorganic salt was removed, the acetic acid filtrate concentrated to a small volume and the slurry formed triturated thoroughly with ethanol to yield 49 grams of sodium salt.
- the sodium salt prepared as above (24 g.) was dissolved in 1800 ml. water. The solution was filtered and 50 m1. of 29% aqueous ethyl mercuri acetate was added to the filtrate. The crude product precipitated rapidly in high yield and was purified by crystallization from acetone. The pure product was a crystalline solid melting at 226-227 C. with decomposition.
- the product of the present invention as prepared in the foregoing example is useful in the control of fungus.
- the following experimental data will illustrate the fungitoxic character of 5-(p-ethylmercurisulfonylphenyl)-1,2, 3,4,7,7-hexachlorobicyclo-(2.2.1)-2-heptene when applied to common and harmful fungus cultures.
- the concentration of fungicide in the following table was 20 parts per million.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
United States Patent Oflice Patented May 28, 1.957
HALOGENATED MERCURISULFONATES Sidney B. Richter, Chicago, Ill., assignor to Velsicol Chemical Corporation, a corporation of Illinois No Drawing. Application January 22, 1954, Serial No. 405,657
2 Claims. (Cl. 260-433) This invention relates to a new fungicidal composition of matter. Specifically, the present invention relates to -(p-ethylmercurisulfonylphenyl) 1,2,3,4,7,7 hexachlorobicyclo-(2.2.1)-2-heptene having the structure:
Cl H H 01 l @gomgom.
I (BT01 H H I Cl and to its use in the control of fungus infestations.
The composition of the present invention is useful in low concentrations of from 5 to 25 parts per million in controlling tomatoe anthracnose (Colletotrichum phamoides), watermelon end rot (Diplodia natelen sis), barley stripe disease (Helminthosporium gramineum), citrus stem rot (PhomOpsis citri), tomatoe early blight (Alternaria solani), and crown and root rot of alfalfa and soybeans (Rhizoctonia solani).
The product of the present invention may be prepared from sulfonyl chlorides or sulfonyl fluorides of S-phenyll,2,3,4,7,7-hexachlorobicyclo-(2.2.1 -2-heptene described in the copending application of Percy B. Polen, Serial No. 405,658, filed Jan. 22, 1954, now Patent No. 2,712,030. Such sulfonyl halides are treated with sodium acetate to prepare the sodium salt and the sodium salt reacted with ethyl mercuri acetate or any ethyl mercun' salt to form the ethyl mercuri sulfonate compound of the present invention. The following specific example will illustrate the preparation of the present product:
A mixture comprising 47.5 g. (0.1 mole) of 5-(pchlorosulfonylphenyl) 1,2,3,4,7 ,7 hexachlorobicyclo- (2.2.1)-2-heptene, 100 ml. glacial acetic acid, and 16 g. (0.2 mole) of sodium acetate was heated at reflux for three hours. The inorganic salt was removed, the acetic acid filtrate concentrated to a small volume and the slurry formed triturated thoroughly with ethanol to yield 49 grams of sodium salt.
The sodium salt prepared as above (24 g.) was dissolved in 1800 ml. water. The solution was filtered and 50 m1. of 29% aqueous ethyl mercuri acetate was added to the filtrate. The crude product precipitated rapidly in high yield and was purified by crystallization from acetone. The pure product was a crystalline solid melting at 226-227 C. with decomposition.
The product of the present invention as prepared in the foregoing example is useful in the control of fungus. The following experimental data will illustrate the fungitoxic character of 5-(p-ethylmercurisulfonylphenyl)-1,2, 3,4,7,7-hexachlorobicyclo-(2.2.1)-2-heptene when applied to common and harmful fungus cultures. The test utilized is a thread plate evaluation, and numbers indicate the colonies developing after six days of incubation. Letters after the numbers indicate the size of the colony as follows: L= large; M=medium; S=small; VS=very small. The concentration of fungicide in the following table was 20 parts per million.
5-(p-ethylmercurlsulfonylphenyl) 1, 2, 3, 4, 7, 7-hexachlorobicyclo- (2.2.1)-2-heptene Culture Colletotrlchum phomoidee Di lodia 'natelensis He minthosporium gm Phomopsis cz'tn' Xanthomonas phaseoli References Cited in the file of this patent UNITED STATES PATENTS Bowles Nov. 18, 1952 Polen et a1. Mar. 23, 1954
Claims (1)
1. AS A NEW COMPOSITION OF MATTER HAVING THE FOLLOWING STRUCTURE:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US405657A US2794038A (en) | 1954-01-22 | 1954-01-22 | Halogenated mercurisulfonates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US405657A US2794038A (en) | 1954-01-22 | 1954-01-22 | Halogenated mercurisulfonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2794038A true US2794038A (en) | 1957-05-28 |
Family
ID=23604640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US405657A Expired - Lifetime US2794038A (en) | 1954-01-22 | 1954-01-22 | Halogenated mercurisulfonates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2794038A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201115B (en) * | 1961-01-17 | 1965-09-16 | Hooker Chemical Corp | Fungicidal and nematicidal pesticides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618645A (en) * | 1948-11-12 | 1952-11-18 | Bowles Albert Frank | Organic mercurials |
| US2673172A (en) * | 1952-11-25 | 1954-03-23 | Arvey Corp | Fungicidal 1, 2, 3, 4, 7, 7-hexachloro-5-(aminophenyl)-bicyclo-[2.2.1]-2-heptene |
-
1954
- 1954-01-22 US US405657A patent/US2794038A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618645A (en) * | 1948-11-12 | 1952-11-18 | Bowles Albert Frank | Organic mercurials |
| US2673172A (en) * | 1952-11-25 | 1954-03-23 | Arvey Corp | Fungicidal 1, 2, 3, 4, 7, 7-hexachloro-5-(aminophenyl)-bicyclo-[2.2.1]-2-heptene |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201115B (en) * | 1961-01-17 | 1965-09-16 | Hooker Chemical Corp | Fungicidal and nematicidal pesticides |
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